4-(4-chlorobenzyl)-6-phenylpyridazin-3(2H)-one | 58050-61-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-(4-chlorobenzyl)-6-phenylpyridazin-3(2H)-one
• 英文别名: 4-(4-chloro-benzyl)-6-phenyl-2H-pyridazin-3-one；5-[(4-chlorophenyl)methyl]-3-phenyl-1H-pyridazin-6-one
• CAS: 58050-61-6
• 化学式: C₁₇H₁₃ClN₂O
• 分子量: 296.756
• InChiKey: AAYNFNLOALFBEQ-UHFFFAOYSA-N

物化性质

• 熔点：
  202-203 °C(Solv: ethanol (64-17-5))
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(4-chlorobenzyl)-6-phenylpyridazin-3(2H)-one 在 sodium dichromate 、 三氯氧磷 作用下， 以 溶剂黄146 为溶剂， 反应 9.5h， 生成 (4-Chloro-phenyl)-(3-chloro-6-phenyl-pyridazin-4-yl)-methanone
  参考文献：
  名称：

  Ismail, M. F.; Sayed, F. S.; Emara, S. A., Zeitschrift fur Naturforschung, B: Chemical Sciences, 1991, vol. 46, # 12, p. 1720 - 1722

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-3-(4-chlorobenzylidene)-5-phenylfuran-2(3H)-one 在 sodium hydroxide 、 一水合肼 作用下， 以 乙醇 、 正丁醇 为溶剂， 反应 1.0h， 生成 4-(4-chlorobenzyl)-6-phenylpyridazin-3(2H)-one
  参考文献：
  名称：

  3-Aminopyridazine derivatives with atypical antidepressant, serotonergic and dopaminergic activities

  摘要：

  Minaprine [3-[(beta-morpholinoethyl)amino]-4-methyl-6-phenylpyridazine dihydrochloride] is active in most animal models of depression and exhibits in vivo a dual dopaminomimetic and serotoninomimetic activity profile. In an attempt to dissociate these two effects and to characterize the responsible structural requirements, a series of 47 diversely substituted analogues of minaprine were synthesized and tested for their potential antidepressant, serotonergic, and dopaminergic activities. The structure-activity relationships show that dopaminergic and serotonergic activities can be dissociated. Serotonergic activity appears to be correlated mainly with the substituent in the 4-position of the pyridazine ring whereas the dopaminergic activity appears to be dependent on the presence, or in the formation, of a para-hydroxylated aryl ring in the 6-position of the pyridazine ring.

  DOI：

  10.1021/jm00123a004

文献信息

• Synthesis of multi-functional alkenes via Wittig reaction with a new-type of phosphorus ylides
  作者：Yi-Ling Tsai、Siang-en Syu、Shu-Mei Yang、Utpal Das、Yu-Shiou Fan、Chia-Jui Lee、Wenwei Lin

  DOI：10.1016/j.tet.2014.06.015

  日期：2014.8

  A Bu3P-mediated mild and efficient synthesis of multi-functional alkenes has been described starting from substituted acrylate with aldehydes. In situ generated zwitterionic intermediates underwent proton-exchange to afford ylide intermediates, which were trapped by corresponding aldehydes providing the products in up to 92% yield with complete E-stereoselectivity. Further derivatization of the products

  已经描述了Bu 3 P介导的温和而有效的多功能烯烃的合成，该合成是从用醛取代的丙烯酸酯开始的。原位生成的两性离子中间体进行质子交换，以提供叶立德中间体，该中间体被相应的醛捕获，从而以最高92％的收率提供具有完全E-立体选择性的产物。进行产物的进一步衍生化以提供功能性哒嗪酮。
• Synthesis, Spectroscopic Characterization, Antibacterial Activity, and Computational Studies of Novel Pyridazinone Derivatives
  作者：Said Daoui、Şahin Direkel、Munjed M. Ibrahim、Burak Tüzün、Tarik Chelfi、Mohammed Al-Ghorbani、Mustapha Bouatia、Miloud El Karbane、Anass Doukkali、Noureddine Benchat、Khalid Karrouchi

  DOI：10.3390/molecules28020678

  日期：——

  In this work, a novel series of pyridazinone derivatives (3-17) were synthesized and characterized by NMR (1H and 13C), FT-IR spectroscopies, and ESI-MS methods. All synthesized compounds were screened for their antibacterial activities against Staphylococcus aureus (Methicillin-resistant), Escherichia coli, Salmonella typhimurium, Pseudomonas aeruginosa, and Acinetobacter baumannii. Among the series

  在这项工作中，合成了一系列新型哒嗪酮衍生物 (3-17)，并通过 NMR（1H 和 13C）、FT-IR 光谱和 ESI-MS 方法对其进行了表征。筛选了所有合成化合物对金黄色葡萄球菌（耐甲氧西林）、大肠杆菌、鼠伤寒沙门氏菌、铜绿假单胞菌和鲍曼不动杆菌的抗菌活性。在该系列中，发现化合物 7 和 13 对金黄色葡萄球菌 (MRSA)、铜绿假单胞菌和鲍曼不动杆菌具有活性，最低 MIC 值范围为 3.74-8.92 µM。随后，进行了B3LYP/6-31++G(d,p)能级的DFT计算，以研究合成化合物的几何结构、前沿分子轨道、分子静电势图和能隙能。此外，这些化合物对各种细菌蛋白质的活性与分子对接计算进行了比较。最后，进行 ADMET 研究以研究将目标化合物用作药物的可能性。
• WERMUTH, CAMILLE-GEORGES;SCHLEWER, GILBERT;BOURGUIGNON, JEAN-JACQUES;MAGH+, J. MED. CHEM., 32,(1989) N, C. 528-537
  作者：WERMUTH, CAMILLE-GEORGES、SCHLEWER, GILBERT、BOURGUIGNON, JEAN-JACQUES、MAGH+

  DOI：——

  日期：——
• AWAD W. I.; HASHEM A. I.; EL-BADRY K., INDIAN J. CHEM. <IJOC-AP>, 1975, 13, NO 11, 1139-1141
  作者：AWAD W. I.、 HASHEM A. I.、 EL-BADRY K.

  DOI：——

  日期：——
• 3-Aminopyridazine derivatives with atypical antidepressant, serotonergic and dopaminergic activities
  作者：Camille Georges Wermuth、Gilbert Schlewer、Jean Jacques Bourguignon、Georges Maghioros、Marie Jeanne Bouchet、Claudine Moire、Jean Paul Kan、Paul Worms、Kathleen Biziere

  DOI：10.1021/jm00123a004

  日期：1989.3

  Minaprine [3-[(beta-morpholinoethyl)amino]-4-methyl-6-phenylpyridazine dihydrochloride] is active in most animal models of depression and exhibits in vivo a dual dopaminomimetic and serotoninomimetic activity profile. In an attempt to dissociate these two effects and to characterize the responsible structural requirements, a series of 47 diversely substituted analogues of minaprine were synthesized and tested for their potential antidepressant, serotonergic, and dopaminergic activities. The structure-activity relationships show that dopaminergic and serotonergic activities can be dissociated. Serotonergic activity appears to be correlated mainly with the substituent in the 4-position of the pyridazine ring whereas the dopaminergic activity appears to be dependent on the presence, or in the formation, of a para-hydroxylated aryl ring in the 6-position of the pyridazine ring.